HCID 89726145, compound → HCID 178492996, compound

HRID 591979Notes

Reaction equation

HRID 591979 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[CH:5]=[CH:4][N:3]=1.[CH3:20][O:21][C:22]1[CH:29]=[C:28]([N:30]2[CH2:35][CH2:34][CH:33]([N:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)[CH2:32][CH2:31]2)[CH:27]=[CH:26][C:23]=1[CH:24]=O>>[CH3:20][O:21][C:22]1[CH:29]=[C:28]([N:30]2[CH2:35][CH2:34][CH:33]([N:36]3[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]3)[CH2:32][CH2:31]2)[CH:27]=[CH:26][C:23]=1[C:24]1[NH:1][C:2]2=[N:3][CH:4]=[CH:5][C:6]([NH:9][C@@H:10]3[C@@H:15]4[CH2:16][C@@H:12]([CH:13]=[CH:14]4)[C@@H:11]3[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=1

Participants

3

Reactant 2

HCID 89726145HCID 89726145, compoundHCID 117701640(1S,2S,3R,4R)-3-(2,3-Diamino-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178492996HCID 178492996, compoundYield 20%

Procedure

In a similar fashion to Compound LXXXVII, (1S,2S,3R,4R)-3-(2,3-Diamino-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (50.0 mg, 0.193 mmol) and 2-methoxy-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-benzaldehyde (67.3 mg, 0.212 mmol) were reacted to produce 19 mg (20%) of the title compound. mp: 185-195° C., 1H NMR (300 MHz, DMSO-d6): 11.84 (s, 1H), 7.99 (d, J=9 Hz, 1H), 7.87 (d, J=5 Hz, 1H), 7.65 (s, 1H), 7.16 (s, 1H), 6.72 (d, J=8 Hz, 1H), 6.67 (d, J=8 Hz, 1H), 6.58 (s, 1H), 6.37 (d, J=5 Hz, 1H), 6.32 (s, 2H), 3.95 (s, 3H), 3.90 (d, J=12 Hz, 2H), 2.87-2.74 (m, 4H), 2.59 (d, J=8 Hz, 1H), 2.33 (m, 4H), 2.23 (d, J=8 Hz, 1H), 2.14 (s, 3H), 1.86 (d, J=12 Hz, 2H), 1.50 (q, J=12 Hz, 2H), 1.42 (d, J=8 Hz, 1H). MS: 557 (M+H), HPLC: 1.58 min (G method).

Sources & evidence

ORD record
ord-7d3423ca5ea04deb8d672b126ea63a59
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

Loading…